Reacción #1181619

Ecuación de reacción

bromocyclopropane

5-bromo-2-chlorophenol

bromocyclopropane

caesium carbonate

HCl

→

title compound

Rendimiento 87.9%

4-Bromo-1-chloro-2-cyclopropoxy-benzene

Rendimiento 87.9%

Disolventes

N,N-dimethylacetamide

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONThe reaction mixture was poured onto ice-water (40 ml)
2. 2
   ExtracciónThis mixture was extracted with TBME (twice 50 ml)
3. 3
   LavadoThe organic layers were washed with brine (40 ml)
4. 4
   Secadodried over sodium sulfate
5. 5
   ConcentraciónConcentration and purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 67:33)

Procedimiento

A mixture of 5-bromo-2-chlorophenol (543 mg, 2.62 mmol), bromocyclopropane (836 μl, 10.47 mmol) and caesium carbonate (1.701 g, 5.24 mmol) in N,N-dimethylacetamide (7.5 ml) was stirred for 47 h at 150° C. After 25.25 h further bromocyclopropane (836 μl, 10.47 mmol) was added. The reaction mixture was poured onto ice-water (40 ml) and set to pH=2 with aqueous HCl (1 N, 9.5 ml). This mixture was extracted with TBME (twice 50 ml). The organic layers were washed with brine (40 ml), combined and dried over sodium sulfate. Concentration and purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 67:33) afforded the title compound (570 mg, 87%) as a light yellow oil. MS m/e: 248.0 [M+H]+

Fuente